Taking some backcountry ski lessons before venturing beyond a resort’s boundaries is a wise idea (I wish I'd taken that approach). Most of the well-known resorts provide at least private lessons, if not group lessons, in off-piste skiing. A handful will even take you past the gates and far into the backcountry. I recommend these programs.
Jackson Hole, Wyoming
Jackson Hole has the country’s premier off-piste ski program. Its backcountry guides lead students into the vast stretches of untracked powder beyond the resort’s boundaries, teaching them safety techniques, transceiver use, group travel, snow science, and the basics of bombing down ungroomed slopes. Students cover 12,000 vertical feet during the full-day lesson. Backcountry Guides also offers trips to Teton Pass (starts at $400 per person for a half day).
Jay Peak, Vermont
Don’t underestimate New England's backcountry. Though it doesn’t have the high elevations of the West, the glade skiing is generally more challenging (and dangerous) because the trees are more tightly packed. Some of the most renowned stretches of off-piste skiing in the East are located the acres of glades at Jay Peak. The resort offers two-hour Glade Clinics for groups of three or more, starting at $45. Be careful about straying out of bounds, though. The resort charges for mountain rescues—and people get lost in the woods there every winter.
Big Sky, Montana
With an average of two skiers per acre on its vast 3,800 acres of slopes, Big Sky makes finding untracked snow easier than just about anywhere else. To see what off-piste heaven looks like, be the first on the Lone Peak Tram in the morning after a big dump. Big Sky Ski School’s mountain guide service will take you anywhere on the mountain, and provide you with the skills and safety training you’ll need to go it alone with your buddies later (starts at $410 for a half day).